The solution conformations of lidocaine analogues

The solution conformations of lidocaine analogues

IR and 1H NMR studies in CDCl3 and CCl4 of a series of tertiary aminoxylidides with the amino group in the 2 to 6 position of the acyl chain are described. Lidocaine, diethylaminoaceto-2',6'-xylidide, forms an intramolecular five-membered ring hydrogen-bonded monomer at all concentrations...

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Bibliographic Details
Published in:Pharmaceutical research Vol. 8; no. 8; pp. 1013 - 1020
Main Authors: MCMASTER, P. D, NORIS, V. J, STANKARD, C. E, BYRNES, E. W, GUZZO, P. R
Format: Journal Article
Language:English
Published: New York, NY Springer 01-08-1991
Subjects:
Analysis
Biological and medical sciences
Carbon Tetrachloride
Chloroform
General pharmacology
Lidocaine - analogs & derivatives
Lidocaine - chemistry
Medical sciences
Molecular Conformation
Pharmacology. Drug treatments
Solutions
Local anesthetic
Infrared spectrometry
Chloroform
Partition coefficient
NMR spectrometry
Solution
Conformation
Hydrogen bond
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Summary:IR and 1H NMR studies in CDCl3 and CCl4 of a series of tertiary aminoxylidides with the amino group in the 2 to 6 position of the acyl chain are described. Lidocaine, diethylaminoaceto-2',6'-xylidide, forms an intramolecular five-membered ring hydrogen-bonded monomer at all concentrations in both solvents. beta-Diethyl-amino-propiono-2',6'-xylidide forms an intramolecular six-membered ring hydrogen-bonded monomer in CDCl3 and CCl4 but a trans intermolecularly associated species is the major form present at high concentrations in CCl4. The longer-chain homologues are mixtures of nonassociated trans and cis monomers at low concentrations but associated trans forms predominate at high concentrations. Evidence for the presence of a hydrogen-bonded seven-membered ring intramolecular monomer in CDCl3 for gamma-diethylaminobutyro-2',6'-xylidide is presented. The relationship between the molecular conformation and the partition coefficient is discussed.
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ISSN:0724-8741
1573-904X
DOI:10.1023/A:1015805023987